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Record Information
Version2.0
Created at2022-03-17 21:13:15 UTC
Updated at2022-03-17 21:13:15 UTC
NP-MRD IDNP0049483
Secondary Accession NumbersNone
Natural Product Identification
Common Nameb-D-Glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose
DescriptionB-D-Glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose, also known as b-D-glucopyranuronosyl-(1->3)-a-D-galactopyranuronosyl-(1->2)-6-deoxy-L-mannose, 9CI, belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. B-D-Glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, b-D-Glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose has been detected, but not quantified in, several different foods, such as coffee and coffee products, fats and oils, fruits, and green vegetables. b-D-Glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose is found in Abelmoschus esculentus , Abelmoschus manihot and Okra mucilage. This could make b-D-glucuronopyranosyl-(1->3)-a-D-galacturonopyranosyl-(1->2)-L-rhamnose a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
b-D-Glucopyranuronosyl-(1->3)-a-D-galactopyranuronosyl-(1->2)-6-deoxy-L-mannose, 9ciHMDB
6-({2-carboxy-3,5-dihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxan-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC18H28O17
Average Mass516.4047 Da
Monoisotopic Mass516.13265 Da
IUPAC Name4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,5-dihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid
Traditional Name4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,5-dihydroxy-6-[(2,4,5-trihydroxy-6-methyloxan-3-yl)oxy]oxane-2-carboxylic acid
CAS Registry Number13283-31-3
SMILES
CC1OC(O)C(OC2OC(C(O)C(OC3OC(C(O)C(O)C3O)C(O)=O)C2O)C(O)=O)C(O)C1O
InChI Identifier
InChI=1S/C18H28O17/c1-2-3(19)5(21)13(16(30)31-2)35-18-9(25)10(8(24)12(34-18)15(28)29)32-17-7(23)4(20)6(22)11(33-17)14(26)27/h2-13,16-25,30H,1H3,(H,26,27)(H,28,29)
InChI KeyZQXWNXNNCNMCTA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusPlant
Abelmoschus manihotPlant
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Okra mucilage-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Pyran
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-4.8ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area282.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.94 m³·mol⁻¹ChemAxon
Polarizability45.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0039728
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019367
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75069229
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available